Methanol → HCID 57421799, compound

HRID 2074234Notes

Reaction equation

HRID 2074234 reaction equation
CO.[ClH:3].[NH:4]1[CH2:9][CH2:8][CH:7](/[CH:10]=[CH:11]/[C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=2)[CH2:6][CH2:5]1.[H][H]>[C].[Pd].O>[ClH:3].[NH:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([NH2:18])=[O:17])=[CH:19][CH:20]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 887MethanolHCID 57462244HCID 57462244, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57421799HCID 57421799, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

10% Palladium-carbon (catalytic amount) was added to a methanol (15 ml)/water (5 ml) solution containing 4-[(E)-2-piperidin-4-ylvinyl]benzamide hydrochloride (800 mg), followed by stirring in a hydrogen gas atmosphere at room temperature under normal pressure for 4 hours. The catalyst was removed by filtration, and the resulting filtrate was concentrated under reduced pressure. The resulting solid was recrystallized from ethanol/acetonitrile to obtain 4-(2-piperidin-4-ylethyl)benzamide hydrochloride (451 mg) (Reference Example 58).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe resulting filtrate was concentrated under reduced pressure
  3. customThe resulting solid was recrystallized from ethanol/acetonitrile

Sources & evidence

ORD record
ord-4a94db12aee7431688334d7708f83753
Source dataset
uspto-grants-2011_04
Patent number
US07919494B2

Reaction notes

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